1995•Journal of the Chemical Society Perkin Transactions 2Requires access
A study of the mechanism of solvoysis of but-3-enyl bromide (4-bromobut-1-ene) using the extended (two-term) Grunwald–Winstein equation
Dennis N. Kevill, Mohamad H. Abduljaber
Open publisher page 3 citations
Abstract
The solvolysis of but-3-enyl bromide at 70 °C follows the SN2 mechanism over a wide variety of solvent as indicated by a sensitivity to changes in solvent nucleophilicity (l value) of 0.99 ± 0.04, specific rates of solvolysis of about on-half of those for the saturated butyl bromide and a kOTs/kBr ratio in ethanol of 12, essentially indentical with the value previously observed for ethanolyses of methyl and ethyl derivatives. There are indications of a minor (about 35%) SN1 component to the solvolysis in 97% TFE, which becomes dominant in 90% HFIP. Kinetic analysis suggest, consistent with previous product studies, only an approximately 4% SN2 component to a dominant SN1 formolysis of the corresponding tosylate.